You can never go wrong with a pair of Chelsea Boots ($120), especially from Steve Madden. They’re designed with a round toe, chunky block heel, lug sole, and pull tabs for easy on-, off- maneuvering.

Prices start at just $14. When you’re packing for a warm-weather vacation, it can be tempting to bring your most impractical (yet fabulous) sandals. Unfortunately, you’ll likely be riddled with foot ...